Acetic Acid → 4-Biphenyl-3-yl-1,3-dihydro-indol-2-one

HRID 1839617Notes

Reaction equation

HRID 1839617 reaction equation
[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH:9]=[CH:10][NH:11]3)[CH:2]=1.C([OH:24])C.C(O)(=O)C.[Br-].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>CC(O)(C)C.[Zn]>[C:1]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH2:9][C:10](=[O:24])[NH:11]3)[CH:2]=1

Participants

7

Reactant 4

HCID 176Acetic Acid2×HCID 702EthanolHCID 21124087PyridiniumtribromideHCID 225618024-biphenyl-3-yl-1H-indole

Product 1

HCID 225616924-Biphenyl-3-yl-1,3-dihydro-indol-2-oneYield 72%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6386tert-ButanolSolvent

Procedure

To the suspension of 4-bipheny-3-yl-1H-indole (3.5 g, 13 mmol) in t-BuOH:ethanol:acetic acid (82 mL:49 mL:269 mL) was added pyridinium tribromide (12.7 g, 40 mmol) portionwise. The mixture was stirred at room temperature for 3 hours, and then to the mixture was added acetic acid (63 mL). Zinc dust (4.39 g, 67 mmol) was added to the reaction mixture portionwise. After stirring for one hour, any unreacted zinc was filtered off and most of the solvent was removed under reduced pressure. The residue was diluted with ethyl acetate, washed with water (3×), sat. NaHCO3, brine, dried over Na2SO4, concentrated and triturated with ether to give 2.67 g (72%) of 4-biphenyl-3-yl-1,3-dihydro-indol-2-one.

Workup

  1. stirringAfter stirring for one hour
  2. filtrationany unreacted zinc was filtered off and most of the solvent
  3. customwas removed under reduced pressure
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with water (3×), sat. NaHCO3, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customtriturated with ether

Sources & evidence

ORD record
ord-a2c52ea628d748d48712ccb9171fff43
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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